Ruthenium- and enzyme-catalyzed dynamic kinetic resolution of secondary alcohols

Journal of the American Chemical Society

Volumn 121, Issue 8, 1999, Pages 1645-1650

  Persson, B Anders ^a   Larsson, Anna L E ^a   Le Ray, Mikaël ^b   Bäckvall, Jan E ^b  

^a UPPSALA UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALCOHOL; RUTHENIUM;

ARTICLE; CANDIDA; CATALYSIS; CATALYST; ENANTIOMER; ENZYME ACTIVITY; ENZYME MECHANISM; HYDROLYSIS; RACEMIC MIXTURE; SYNTHESIS;

EID: 0033518869     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983819+     Document Type: Article

References (111)

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79. For other solvent studies using Novozym 435, see refs 17a, 18f, and 18i.
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81. This electronic effect has been seen by others in ruthenium-catalyzed asymmetric transfer hydrogenation reactions: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
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98. The ethanol or 2-propanol formed is then acylated by the enzyme, and the process becomes irreversible.
99. Waagen, V.; Partali, V.; Hollingsaeter, I.; Huang, M. S. S.; Anthonsen, T. Acta Chem. Scand. 1994, 48, 506.
100. Stephenson, O. J. Chem. Soc. 1954, 1571. See also ref 19b.
101. Beller, M. Unpublished results from these laboratories.
102. The separation of 1-phenylethyl acetate (4) and 4-chlorophenyl acetate is difficult, and in most cases only unreacted 1-phenylethanol (3) was separated in this purification. The hydrolysis was performed on the mixture of (R)-1-phenylethyl acetate and 4-chlorophenyl acetate, and the (R)-1-phenylethanol was isolated in the purification after the hydrolysis step.
103. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.
104. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.
105. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.
106. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.
107. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.
108. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.
109. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.
110. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.
111. NMR data can be found in the following references. 4: Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531. 7: Pincock, J. A.; Wedge, P. J. J. Org. Chem. 1995, 60, 4067. 9: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H. J. Chem. Soc, Perkin Trans. 1 1996, 1, 67. 13: Brown, S. M.; Davies, S. G.; de Sousa, J. A. A. Tetrahedron: Asymmetry 1993, 4, 813. 15: Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1976, 41, 801. 17: Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235. 19: Rao, B. R.; Nambudiry, M. E. N. Synth. Commun. 1991, 21, 1721. 21: Funahashi, K. Bull. Chem. Soc. Jpn. 1979, 52, 1488. 25: See ref 22b. 29: Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155.